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Details

Stereochemistry ABSOLUTE
Molecular Formula C57H65F5N10O8
Molecular Weight 1113.1824
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIBRENTASVIR

SMILES

C[C@]([H])([C@@]([H])(C(=O)N1CCC[C@@]1([H])c2nc3cc(c(cc3[nH]2)F)[C@@]4([H])CC[C@]([H])(c5cc6c(cc5F)[nH]c([C@]7([H])CCCN7C(=O)[C@]([H])([C@@]([H])(C)OC)N=C(O)OC)n6)N4c8cc(c(c(c8)F)N9CCC(CC9)c%10ccc(cc%10)F)F)N=C(O)OC)OC

InChI

InChIKey=VJYSBPDEJWLKKJ-NLIMODCCSA-N
InChI=1S/C57H65F5N10O8/c1-29(77-3)49(67-56(75)79-5)54(73)70-19-7-9-47(70)52-63-41-25-35(37(59)27-43(41)65-52)45-15-16-46(72(45)34-23-39(61)51(40(62)24-34)69-21-17-32(18-22-69)31-11-13-33(58)14-12-31)36-26-42-44(28-38(36)60)66-53(64-42)48-10-8-20-71(48)55(74)50(30(2)78-4)68-57(76)80-6/h11-14,23-30,32,45-50H,7-10,15-22H2,1-6H3,(H,63,65)(H,64,66)(H,67,75)(H,68,76)/t29-,30-,45-,46-,47+,48+,49+,50+/m1/s1

HIDE SMILES / InChI

Molecular Formula C57H65F5N10O8
Molecular Weight 1113.1824
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Pibrentasvir is a direct acting antiviral agent and Hepatitis C virus (HCV) NS5A inhibitor that targets the the viral RNA replication and viron assembly. NS5A is a phosphoprotein that plays an essential role in replication, assembly and maturation of infectious viral proteins. The basal phosphorylated form of NS5A, which is maintained by C-terminal serine cluster, is key in ensuring its interaction with the viral capsid protein, or the core protein. By blocking this interaction, pibrentasvir inhibits the assembly of proteins and production of mature HCV particles. In the United States and Europe, Pibrentasvir is approved for use with glecaprevir as the combination drug glecaprevir/pibrentasvir (trade name Mavyret in the US and Maviret in the EU) for the treatment of hepatitis C. This fixed-dose combination therapy was FDA-approved in August 2017 to treat adults with chronic hepatitis C virus (HCV) genotypes 1-6 without cirrhosis (liver disease) or with mild cirrhosis, including patients with moderate to severe kidney disease and those who are on dialysis.

CNS Activity

Curator's Comment:: [14C]pibrentasvir did not cross the blood:brain barrier at levels above the QWBA lower quantitation limit of 48.5 ng eq/g.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAVYRET

Approved Use

MAVYRET is indicated for the treatment of adult patients with chronic hepatitis C virus (HCV) genotype 1, 2, 3, 4, 5 or 6 infection without cirrhosis or with compensated cirrhosis (Child-Pugh A). MAVYRET is also indicated for the treatment of adult patients with HCV genotype 1 infection, who previously have been treated with a regimen containing an HCV NS5A inhibitor or an NS3/4A protease inhibitor (PI), but not both.

Launch Date

1501632000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
31 ng/mL
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
324 ng/mL
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9.68 ng/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
123 ng/mL
180 mg 1 times / day multiple, oral
dose: 180 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.1 ng/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
167 ng/mL
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
18.3 ng/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.63 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
223 ng/mL
405 mg single, oral
dose: 405 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
343 ng/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
71.7 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
64.4 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
87.1 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
180 ng × h/mL
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2170 ng × h/mL
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
54.5 ng × h/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
881 ng × h/mL
180 mg 1 times / day multiple, oral
dose: 180 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.56 ng × h/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1040 ng × h/mL
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
118 ng × h/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.6 ng × h/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1630 ng × h/mL
405 mg single, oral
dose: 405 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2560 ng × h/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
408 ng × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
474 ng × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
594 ng × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20.8 h
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.1 h
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.9 h
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
22.5 h
180 mg 1 times / day multiple, oral
dose: 180 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.8 h
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.4 h
240 mg single, oral
dose: 240 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
14.8 h
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.6 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
17.7 h
405 mg single, oral
dose: 405 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
14.4 h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.9 h
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
17.7 h
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
14.5 h
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIBRENTASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
unknown, oral
PIBRENTASVIR plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg 1 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 18-55 years
Health Status: healthy
Age Group: 18-55 years
Sex: M+F
Sources:
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
healthy, 18-55 years
Health Status: healthy
Age Group: 18-55 years
Sex: M+F
Sources:
Sourcing
PubMed

PubMed

TitleDatePubMed
Efficacy of Glecaprevir/Pibrentasvir for 8 or 12 Weeks in Patients With Hepatitis C Virus Genotype 2, 4, 5, or 6 Infection Without Cirrhosis.
2018 Mar
Patents

Patents

Sample Use Guides

MAVYRET is a fixed-dose combination product containing glecaprevir 100 mg and pibrentasvir
Route of Administration: Oral
According to HCV replicon assays, pibrentasvir has EC50 values ranging from 0.08-4.6 nM agaisnt laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4d, 5a, and 6a, or EC50 values of 0.5-4.3 pM against laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4b, 4d, 5a, 6a, 6e and 6p.
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:37:33 UTC 2021
Edited
by admin
on Sat Jun 26 01:37:33 UTC 2021
Record UNII
2WU922TK3L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIBRENTASVIR
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
ABT-530
Code English
MAVYRET COMPONENT PIBRENTASVIR
Common Name English
PIBRENTASVIR [ORANGE BOOK]
Common Name English
PIBRENTASVIR [USAN]
Common Name English
PIBRENTASVIR [JAN]
Common Name English
PIBRENTASVIR [MI]
Common Name English
DIMETHYL N,N'-(((2R,5R)-1-(3,5-DIFLUORO-4-(4-(4-FLUOROPHENYL)PIPERIDIN-1-YL)PHENYL)PYRROLIDINE-2,5-DIYL)BIS((6-FLUORO-1H-BENZIMIDAZOLE-5,2-DIYL)((2S)-PYRROLIDINE-2,1-DIYL)((2S,3R)-3-METHOXY-1-OXOBUTANE-1,2-DIYL)))BISCARBAMATE
Systematic Name English
A-1325912.0
Code English
PIBRENTASVIR [INN]
Common Name English
PIBRENTASVIR [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000191256
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
WHO-ATC J05AP57
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
FDA ORPHAN DRUG 550516
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C166601
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
CAS
1353900-92-1
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
ChEMBL
CHEMBL3545123
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
FDA UNII
2WU922TK3L
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
DRUG BANK
DB13878
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
MERCK INDEX
M12027
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
LACTMED
Pibrentasvir
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
DRUG CENTRAL
5244
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
PUBCHEM
58031952
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
INN
10260
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
RXCUI
1940636
Created by admin on Sat Jun 26 01:37:33 UTC 2021 , Edited by admin on Sat Jun 26 01:37:33 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Blood-to-Plasma Ratio PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC